Carbanilic acid derivatives



Patented Mar. 1, 1938 UNITED STATES CARBANILIC ACID DERIVATIVES William A. Lott,

Braker, Brooklyn,

Newark, N. J., and William N. Y., assignors to E. R.

Squibb & Sons, New York, N. Y., a corporation of New York No Drawing. Application August 30, 1933, Serial No. 687,482 3 7 Claims.

This invention relates to, and has for its object the provision of, certain carbanilic acid derivatives and an intermediate compound.

Compositions of this invention comprise compounds having the general formula XNHCOORN 2 wherein X is phenyl or substituted phenyl, R is an alkylene, Y is an alkyl or an aralkyl, and Z is an alkyl or an aralkyl, different from Y, which compounds may be prepared by reacting /Y HORN z with XNCO (or with XNCClz Examples 1. Beta-(N-normal-amyl N-ethyl aminol-ethyl carbanilate hydrochloride,

/CzH OaHaNHCOOOHzCHzN .HCI

o n 11 g. of normal-amyl ethyl amine (which may be prepared by the method of Carothers, J. A. C. S. 49, 2913), 12 g. of anhydrous potassium carbonate, and 8 g. of ethylene chlorhydrin are heated together on the steam-bath for one hour, in an oil bath at 134 C. for two hours, and at 150-155 C. for half an hour. When completion of the reaction is indicated by cessation of evolution of carbon dioxide, the mixture is extracted with ether and the extract is fractionated. There is secured beta-(N-normal-amyl N-ethyl amino)- ethanol, a colorless oil boiling at 210-213 C./760 mm.

2.3 g. of this oil and 1.72 g. of phenyl isocyanate are dissolved in 30- cc. of dry benzene and refiuxed for five hours on the steam-bath; and by the addition of ether-hydrogen-chloride the desired composition is caused to separate out as a white powder having a melting point of 177- 178 C. 5

The base is a colorless oil.

By evaporating a solution containing 3.0 g. of the base and 3.15 g. of boric acid, the borate of the base is obtained.

2. Beta-(N-methyl N-phenethyl amino)-ethy1 carbanilate hydrochloride,

/CH3 OaHiNHC o o o H1OHzN\ .Hoi

- omomom, 15 6.2 g. of, beta-(N-methyl N-phenethyl amino)- ethanol and 4.63 g. of phenyl isocyanate are dissolved in 50 cc. of anhydrous ether, and the solution is boiled for threehours under a reflux condenser, moisture being excluded by means of a calcium chloride tube. When the reaction is complete, the addition of a slight excess of a dry ether solution of hydrogen chloride causes the desired composition to separate immediately as a v v l 1ite crystalline substance, which, on being washed with dry ether, dried, and recrystallized several times from absolute alcohol, is found to have a melting point of 186-187 C.

Among the other compounds embraced by the .3 invention are those represented by the following formulas, and their salts:

/CH3 CsH5NHCOOCH2CH2CH2N CHnCHaCoHu CH3 oflnlNnoooomom on; CHgCHnCuHs 40 camunoooomonm v Q-HzcHaoo n odmNncooomomN ([JHOHzCHzCeHi CgHL CQHBNHC O CHzCHaN CaH7 CsHsNHC O 0 CHaC HzN C4Ha CgHgNHCOOCHaCHsCHgN CQ J CQHENHC O O CHaCHN CH: C4110 CeHsNHC O O CHzGHN CgHs CH CHQJHa):

CH CH:

C5H5NHC O O CHQC CHzN CaHaNHC O O CHOHCHQN Ca n 01H: NBC 0 O C2H4N CaHu NHC O O CIHAN cz lcoHs CH: NHC O O CzH4N C2H4C5Hl CH: NHC O O ciHlN CIHiCuHs wherein X is one of the group phenyl, alkylphenyl, alko-xy-phenyl, and phenyl-phenyl, R. is one of the group alkylene and alkylated alkylene, Y is one of the group methyl and ethyl, and Z is one of the group butyl, amyl, and phenethyl; and the inorganic acid salts thereof.

2. Compounds selected from the class consisting of bases having the general formula:

/Y XNHCOORN wherein X is one of the group phenyl, alkylphenyl, alkoxy-phenyl, and phenyl-phenyl, R is one of the group ethylene and alkylated ethylene, Y is one of the group methyl and ethyl,

and Z is one of the group butyl, amyl, and phenethyl; and the inorganic acid salts thereof.

3. Compounds selected from the class consisting of bases having the general formula:

XNHC O 0 RN wherein X is phenyl, R. is one of the group ethylene and alkylated ethylene, Y is one of the group methyl and ethyl, and Z is one of the group butyl, amyl, and phenethyl; and the inorganic acid salts thereof.

4. Compounds selected from the class consisting of the base beta-(N-normal-amyl N-ethyl amino)-ethyl carbanilate and its inorganic acid salts.

5. Beta-(N-normal-amyl N-ethyl amino) -ethyl carbanilate hydrochloride.

6. Beta-(N-normal-amyl N-ethyl amino) -ethyl carbanilate bo-rate.

7. Beta-(N-methyl N-phenethyl amino) -ethyl carbanilate hydrochloride.

WILLIAM A. LO'I'I'. WILLIAM BRAKER. 

